It is well known that a color development of silver halide color photographic materials causes a reaction of couplers and the oxidation product of a primary aromatic amino color developing agent to form indophenol, indoaniline, indamine, azomethine, phenoxazine, phenazine, and similar dyes, whereby color images are formed. Among the couplers which are used for such silver halide color photographic materials, 5-pyrazolone couplers, cyanoacetophenone couplers, indazolone couplers, pyrazolobenzimidazole couplers, and pyrazolotriazole couplers are used for forming magenta dye images.
Couplers which have hitherto been widely used as magenta dye image-forming couplers and have been studied for use as magenta dye image-forming couplers are mostly 5-pyrazolones. It is known that dyes formed of 5-pyrazolone couplers are excellent in fastness to heat and light, but they do have an yellow component due to the existence of unnecessary absorption near 439 nm, which causes turbidity.
Various magenta dye image-forming coupler skeletones have been proposed, such as pyrazolonebenzimidazole skeletons described in U.K. Pat. No. 1,047,612; indazolone skeletons described in U.S. Pat. No. 3,770,447; and 1H-pyrazolo[3,2-c][1,2,4]triazole skeletons described in U.S. Pat. No. 3,725,067. Furthermore, 1H-imidazo[1,2-b]pyrazole skeletons described in Japanese Patent Application No. 23,434/'83 (corresponding to U.S. patent application Ser. No. 580,303); 1H-pyrazolo[1,5-b][1,2,4]triazolo skeletons described in Japanese Patent Application No. 45,512/'83 (corresponding to U.S. patent application Ser. No. 590,818); 1H-pyrazolo[1,5-d]tetrazole skeleton described in Japanese Patent Application No. 142,801/'83; and 1H-pyrazolo[1,5-b]pyrazole skeletons described in Japanese Patent Application No. 151,354/'83 have more recently been proposed.
The magenta dyes formed of the 1H-pyrazolo[3,2-c][1,2,4]triazole type couplers desxribed in U.S. Pat. No. 3,725,067; U.K. Pat. Nos. 1,252,418 and 1,334,515; the 1H-imidazo[1,2-b]pyrazole type couplers described in Japanese Patent Application No. 23,434/'83; the 1H-pyrazolo[1,5-b][1,2,4]triazole type couplers described in Japanese Patent Application No. 45,512/'83; the 1H-pyrazolo[1,5-d]tetrazole type couplers described in Japanese Patent Application No. 142,801/'83; and the 1H-pyrazolo[1,5-b]pyrazole type couplers described in Japanese Patent Application No. 151,354/'83 in these magenta dye image-forming couplers show excellent absorption characteristics having no unnecessary absorption in the visible wavelength region in a solvent such as ethyl acetate, dibutyl phthalate, etc.
However, the azomethine dyes formed of the 1H-pyrazolo[3,2-c][1,2,4]triazole type couplers among these couplers has very low fastness to light and greatly reduce the properties of color photographic materials, in particular color photographic materials for prints. Other 5-membered-5-membered condensed nitrogen heterocyclic ring type couples form azomethine dyes which also have unsatisfactory light fastness for use in color photographic materials, especially, in print type color photographic materials.
Hetherto, as materials for improving the light fastness of color images composed of azomethine dyes formed of 5-pyrazolone couplers, there are known hydroquinone derivatives described in U.S. Pat. Nos. 3,935,016 and 3,982,944; hydroquinone diether derivatives described in U.S. Pat. No. 4,254,216 and Japanese Patent Application (OPI) No. 21,004/'80; phenol derivatives described in Japanese Patent Application (OPI) No. 145,530/'79; spiroindane derivatives and the methylenedioxybenzene derivatives described in U.K. Patent Publication (unexamined) Nos. 2,077,455 and 2,062,888; the chroman derivatives, spirochroman derivatives, and coumaran derivatives described in U.S. Pat. Nos. 3,764,337; 3,432,300; 3,574,627; and 3,573,050; Japanese Patent Application (OPI) Nos. 152,225/'77; 20,327/'78; and 17,729/'78 (The term "OPI" used herein referes to a "published unexamined Japanese Patent Application.); the hydroquinone monoether derivatives and p-aminophenol derivatives described in Japanese Patent Application (OPI) No. 6321/'80; U.K. Pat. No. 1,347,556; U.K. Patent Publication (unexamined) No. 2,066,975; and Japanese Patent Publication No. 12,337/'79; and the bisphenol derivatives described in Japanese Patent Publication No. 31,625/'73 and U.S. Pat. No. 3,700,455.
These compounds are effective for improving the light fastness of the dye images composed of the azomethine dyes formed of 5-pyrazolone couplers, but although the compounds also show considerable effect for improving the light fastness of the color images composed of the azomethine dyes formed of 5-membered-5-membered condensed nitrogen heterocyclic ring type couplers such as 1H-pyrazolo[3,2-c][1,2,4]triazole couplers, the effect is still insufficient.